


The Bet

by CassieWinchester



Category: Supernatural
Genre: Anal Sex, Angel Castiel, Bets, Bottom Cas, Demon Dean, Demon Tail kink, Foreplay, M/M, Making Out, Mutual Pining, NSFW, Rough Sex, Teasing, Top Dean, Wing Kink, at work, probably reverse as well lol
Language: English
Status: In-Progress
Published: 2018-04-17
Updated: 2018-04-17
Packaged: 2019-04-24 02:15:00
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,938
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14345823
Author URL: https://archiveofourown.org/users/CassieWinchester/pseuds/CassieWinchester
Summary: Alastair, Abaddon and Azazel all have a bet to see who can get the new angel at work into their beds first.  Castiel has just gotten hired at Roman Enterprises, and is the only angel that works there, in a workplace surrounded by demons, vampires and leviathans; not to mention other monsters as well.  The three demons try to get Dean in on the bet, but he refuses as first.  Unbeknownst to his co workers, him and Castiel are already together.  But after talking to his love, they both decide that this bet might be fun, and make up their minds to play along....





	The Bet

**Author's Note:**

> This was a last minute response to a wonderful prompt I found on a destiel fb page by The Dancing Dog. Usually it takes me a LOT longer to plan and write things up, and then I spend an equal amount of time agonizing over it and getting it JUST RIGHT but I didn't really do that with this one so we'll see how this goes. Hope you enjoy!
> 
> Also the first part of this chapter is the prompt that was written by a wonderful inspiring person!

“I bet you guys two hundred dollars I can get that new angel to sleep with me by the end of the month,” smirked Alastair, tail swishing behind him in interest as he eyed up the only angel employed by Roman Enterprises.

Azazel leered at the angel’s soft white wings, gaze roaming over his body greedily.

“I bet you three hundred I can get him to sleep with me.”

Abaddon glanced between both demons contemplatively before slowly turning to the newest member of Roman Enterprises. She smirked in appreciation.

“Three-fifty says he’ll be in my bed by the end of the month.” The female demon turned to Dean. “You want in on this action, Winchester?”

Dean glanced up from his desk. He hadn’t been paying attention because he didn’t particularly enjoy the trio’s company, but he was forced to work beside them on floor ten and the money was good so he wasn’t about to complain.

“Huh?” He asked disinterestedly as he signed yet another document. When would they end?

Azazel flicked his tail in aggravation. “The new floor manager. The only guy in the room with wings? There’s money to be made here if you can get into his pants by the end of the month.” He grinned; an ugly thing that crawled across his face and made Dean want to throw up.

“I’m good, thanks,” Dean said, nose scrunching up in distaste.  
Abaddon sidled up beside him, her cherry tail tangling with Dean’s and all the black-horned demon wanted to do was clamp his staple gun around the thing. She leaned into his personal space and he tried not to gag at whatever toilet water she’d sprayed herself with today.

“Come on, Winchester,” she purred. “This isn’t your average vampire, werewolf or siren… this is something much rarer. An angel. Think of the power thrumming through that body; the grace coursing through those veins… imagine the possibilities. Demon magic meeting angel magic? The sex would be… explosive.”

She ran her fingers through his hair and he leaned away from her with a grimace.

Angels were indeed rare; even more so than demons. However, there were still tensions between the two species, making it difficult for them to work together or even be in the same area as one another sometimes. Centuries of merciless fighting between their ancestors would do that to people.

Truthfully, humans, monsters, angels and demons had only begun to get along within the past century or so. There were still disputes and prejudices and often, they were settled in a less than ideal manner (Dean could still remember the pain in his tail from that wolf bite) but things were gradually getting better and people were at least trying to get along.

Roman Enterprises had hired every creature under the sun except for angels (even its boss was a full-blooded leviathan). That didn’t mean the company was prejudiced against angels, it merely meant that no angels had applied for a job there because they were so few and far between.

Until now.

Castiel Novak was the newest addition to the team. He was highly experienced in matters of business and had acted as manager of several small businesses before becoming CEO at Crowley’s law firm. It wasn’t a huge firm, but it gained him the required credentials for Mr. Roman to take an interest. The leviathan had offered him a job as floor manager (with room to climb the ranks of course) and the extra cash had been too tempting for Novak to resist. Not to mention the idea of being the first angel at the business was highly appealing to someone with Castiel’s ambition.

Dean glanced at the angel for a moment, admiring those snowy wings and the golden halo glowing dimly above his hair, before shaking his head and returning to his paperwork.

“No thanks,” he muttered.

Alastair raised an eyebrow. “What’s the matter, Winchester? You not like angels? I get it and I agree with you, but you have to admit, the sex would be great.”

Dean pulled a face as Azazel rounded his other side.  
“We all know you swing both ways, Dean,” the yellow-tailed demon hummed. “You don’t have to like the guy; just get him into bed and earn a bit of cash. What do you say?”

Dean growled softly in warning, knuckles turning white around his pen.

“Not interested. Make whatever bets you like but count me out.”

“Fine, be a racist,” snorted Abaddon. “But one of us is going to enjoy some oil gland play.” She eyed Castiel hungrily.

Dean shuddered and glowered at her. “He’s not going to sleep with you.”

“Why?” Scoffed Abaddon. “Because I’m a demon? Please. Maybe we’ll have hate sex – I do so enjoy that sort of thing. Or maybe I’ll just roofie his coffee,” she winked.

Alastair chuckled. “Who needs to go to all that effort? A bit of demon magic and he won’t have a clue where he is or where he’s going. Our bet never said anything about him being willing,” he teased and Dean stiffened and snapped his pen from the force of his clenched fists.

“I need a drink,” growled Dean, standing up and stalking away from the trio. As he made his way over to the coffee machine, he could hear them discussing ways of using magic to force the angel into bed with them.

His tail thumped the floor angrily as his eyes slid to black and he didn’t care how many people flinched away from him in fear as he prowled through floor ten. He had to get away from his colleagues.

* * *

Dean scowled at the TV screen. He was still angry from that afternoon despite it being close to eleven P.M. Even Doctor Sexy wasn’t helping to soothe him.

The front door opened and closed quietly and Dean’s eyes slipped shut in relief when someone sat beside him on the couch, a head resting on his shoulder as warm fingers toyed with his tail.

He turned slightly to capture Castiel’s lips.

Once they pulled apart, the angel tilted his head curiously at his black eyes.

“You’re upset,” he stated softly and Dean sighed and stretched over the couch, tugging Castiel on top of him. He wrapped his arms around his lover and pressed his lips to his shoulder.

“The guys at work are pissing me off,” he grumbled.  
Castiel raised a delicate eyebrow and waited patiently for his demon to continue.

“They’re making bets as to who’ll get you into bed first,” Dean growled quietly. “Said they’re gonna use magic to force you.”

Castiel lifted both eyebrows in amusement.

“That’s going to be difficult considering angels aren’t susceptible to demon magic.”

“They don’t know that,” Dean huffed.

Castiel frowned. “Then why does this bother you? I’m clearly not going to sleep with them and their magic can’t force me, so why are you so upset?”

Dean held his angel a little tighter. “…Their magic not working on you isn’t the point. It’s the idea that they’d even think of trying something like that. That they’d do that to you and make a bet over it.”

Castiel mulled the answer over for a moment.

“…I see. You’re worried for me. Possessive.”

Dean kissed his lover’s neck. “I love you,” he corrected gently. “I don’t like the idea of someone hurting you or attempting to hurt you.”

Castiel nodded carefully, dissecting this response.

The problem with angels was they were beautifully flawless, astoundingly intelligent, ambitious, exceedingly talented in any skill they set their minds to… and about as dense as a brick when it came to emotions. That’s why there were so few of them; they spent so long focusing on being perfect at everything that they forgot to find time for love and fun and they often died before they found a partner and had children.

Castiel was learning, thanks to Dean, but it was slow-going at times and Dean had to be incredibly patient.

Fortunately, Castiel taught him how to be that and Dean was not the rage-fuelled, selfish creature demons were known to be, thanks to the angel.

A tiny smirk tugged at Castiel’s lips and it was such a foreign expression that Dean had to do a double-take. It was gone before he had a chance to question it.

“Have they asked you to participate in these wagers?” Asked Castiel innocently and Dean frowned in confusion.

“…Yeah, but I never said yes, obviously.”

There was that tiny smirk again.

“Maybe you should.”

Dean’s eyes widened. Had he heard that correctly?

“Excuse me? Sounded like you said ‘I should’.”

Castiel rolled over to gaze at Dean, eyes sparkling in mischief.

“That’s because I did. You’re certain to win such a bet and not only will you gain money, imagine their expressions when I say yes to you without you ‘forcing’ me to sleep with you.”

Dean gaped. “I’m not treating you as a bet!” He protested but Castiel shook his head with a small smile.

“You’re always trying to find new ways for me to see the fun side of life. I think this could be fun. You could have a second attempt at trying to ‘win’ my affections,” he teased. “A competition with your fellow demons. That’s how your species usually win mates, is it not? Competing to impress them?”

Dean’s demon instincts perked up at that idea. A chance to put Alastair, Azazel and Abaddon in their places?

Castiel claimed his lips heatedly and Dean wondered when his angel had become so skilled at kissing.

“I could put on a show when you win, if you’d like. Show your colleagues exactly who I’m interested in?” Castiel suggested through a whisper and Dean’s tail swished in interest.

Angels were usually reserved creatures but Castiel was offering to stake a claim on Dean in the middle of work, just to humiliate Dean’s disgusting co-workers.

Dean liked that idea very much.

“You’d have to work for my attentions, of course,” hummed Castiel with a playful smirk and Dean wondered if he was dreaming. Who was this awesome angel and what had he done with Cas?

“I can do that,” breathed Dean as he pulled his lover in for another deep kiss.

Castiel smirked against his mouth. “You’re willing to play this… game?”

Dean nodded enthusiastically. “Flirt with you all day and not get in trouble for it? Game on.”

Castiel curled his wings around his lover and Dean purred at their softness.

“I look forward to your... flirtations.”

 

***

 

After consulting one another, Dean and Castiel put thier plan into action the very next day...

 

“Hey guys,”  Dean greeted to the three demons that shared his workspace.  Alastair glanced up from his desk, his eyebrows raised in mild surprise. 

“You talking to us?”  Abaddon asked, putting words to the other two’s thoughts. 

“Who else I would be talking to?”  He watched them exchange glances with amusement as he sat down at his desk. “I want in,”  he continued.

There was a pause.  “On…?”  Azazel pressed, sounding a tad annoyed.

“The bet.  I want in on the bet with the angel.”

Abaddon looked up from her work in interest.  “Oh really?  Because I’ve got a pretty high bet against you and an even better plan Mr. Winchester.” 

“$800 says he’ll be in bed with me by the end of next week,”  Dean smirked.  At that they all stopped what they were doing and gaped at him.

“Ha, in your dreams boy!”  Alastair mocked. 

“I would LOVE to see this,”  Azazel leered, his tail slashing back in forth in interest as Abaddon nodded in agreement. 

“How about this,”  Dean said as he leaned forward in his chair.  “Roman will be throwing the annual company party next Saturday night.  Whoever can get to him by then, the others owe them the $800; sound fair?”  When there was a pause from everyone he added “Unless you guys are too chicken; I’ll just give you a chance to back out now.”

“Deal.”  All three of them said in perfect unison, which is exactly what Dean wanted to hear. 

“Alrighty; better get going then, hadn’t we?”  Dean said as he spotted his angel’s feathery wings not far off, flipping through a filing cabinet with an almost annoyed look on his beautiful face. 

Dean stood up and, with a confident flick of his tail, sauntered up to the angel. The other three watched closely out of the corners of their eyes.  Abaddon’s tail was thrashing back and forth angrily, which only made him more confident.

_Already pissing them off, this is going to be more fun than I thought._   He reached Cas and leaned casually against the tall cabinet, regarding the angel with an almost haughty air. 

“You’re Castiel, right?  I don’t believe we’ve formally met yet.”

Castiel didn’t stop searching through the files as he replied.  “Well, now we have.”   Dean was surprised by his uncaring tone.

“But you don’t even know my name,”  he replied.

“Of course I do Dean; it is my job to know all of the workers of which I am manager of.” 

Dean’s tail twitched in annoyance; what was wrong with Cas?  What had happened to showing off in front of the other dicks sitting at the desks across the room?

He cleared his throat.  “Well, how about joining me for dinner tonight after work then, and we could get to know each other even more, if you know what I mean,”  he cooed, very briefly running his tail across the angel’s feathers and raising his eyebrows suggestively. 

Cas _finally_ stopped looking through the files and glanced up at him, and Dean waited for him to accept his most gracious offer.

“No thank you.”  Came the blatant reply.  Cas plucked a manila colored file out of the cabinet and brushed past him, striding out of the room, those damn wings following gracefully behind him. 

As soon as Cas had left, laughter erupted from his co workers desks.

“That was almost too painful to watch!”  Alastair cackled as he doubled over on his desk.

“That was wonderful,”  Abaddon giggled, jumping up and clinging on to Dean as he walked back to his desk.  “Come to dinner with me, you’ll get to know me even better then…in depth.”  She mimicked, running her spindly sweaty hand over the side of his face and making him lose it. 

“Shut up!”  he growled as he shoved  her away forcefully, his eyes once more turning black.  “You guys have anything more to say to me?”  he threatened, fixing them all with a pitch black stare and a dangerously swishing tail.  He could be downright intimidating like this and all three of them fell silent after that.  “Damn straight.”  He stomped out of the room.  Anger got the best of him then and he sunk his fist into the wall, punching a hole clear through the dry wall. 

_What the Hell was that!?  That was NOT what we talked about last night!_   Still too angry to go back to work, he stalked to the breakroom to cool off and try to make sense of what had just happened.  As he slammed the door behind him, he almost didn’t notice what was sitting on one of the tables.  Moving closer, he realized that it was indeed a fully baked raspberry pie, with a note on it that said “To Horns, from Feathers” on it. 

Horns was the nickname Cas had started calling him after they had gotten together, and while it wasn’t the most creative nickname in the world, Dean secretly loved it because it was his angel that had given it to him.  So he had given him an equally creative nickname back, Feathers.  He grudgingly sat down to eat some of the pie when the door opened and closed behind him. 

“You’ve got guts, showing up in here after what just happened.”  he grumbled, stuffing his face with a fork full of raspberry and crust. 

“You’ve got to be joking Dean,”  Castiel stated as slender but sturdy arms slipped around his chest from behind and soft lips nibbled at his ear. 

“You’re the one with the sick joke; this pie better be an apology.” 

“Dean, they would get suspicious if I just blatantly said yes to such an obvious gesture, don’t you think?  Plus I’m not going to lie, I had expected something a bit more…creative than that.  Didn’t I say that you would have to work for my affections?”  Cass murmured against the side of his neck and Dean cocked his head to the side unconsciously, giving the angel’s lips more room to explore. 

“I guess I _was_ lacking a bit in creativity,”  he grumbled, stuffing another forkful of pie into his mouth. 

“I love you more than anything in this whole universe,”  Cass whispered as he kissed Dean’s  neck. His hands traveled down and under Dean’s shirt, making the demon sigh.  Then it was over as Cas stood back up. 

“Anyway I’ve got to get back to work.  You should too, it’s way too early for anyone to be taking breaks you know.”  Dean spun around as Cas tugged lightly at his tail and gave him a sly smile, and then he was heading out the door and gone. 

_Damn him,_  Dean silently cursed, although a smile was trying to tug its way onto his face.  He wanted him to work for it; fine, he would work for it.  By the party next week, he was going to have that angel on his knees and begging for attention, you could be sure of that.

**Author's Note:**

> Please review! <3


End file.
